US4107196A - N-tertiarybutyl organosilylamides - Google Patents
N-tertiarybutyl organosilylamides Download PDFInfo
- Publication number
- US4107196A US4107196A US05/858,144 US85814477A US4107196A US 4107196 A US4107196 A US 4107196A US 85814477 A US85814477 A US 85814477A US 4107196 A US4107196 A US 4107196A
- Authority
- US
- United States
- Prior art keywords
- radical
- tertiarybutyl
- formula
- methyl
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 claims abstract description 15
- -1 3,3,3-trifluoropropyl Chemical group 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 15
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 abstract description 5
- 238000006884 silylation reaction Methods 0.000 abstract description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract description 2
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 abstract 1
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 abstract 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 101150035983 str1 gene Proteins 0.000 abstract 1
- ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical compound C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- NDVMCQUOSYOQMZ-UHFFFAOYSA-N 2,2-bis(trimethylsilyl)acetamide Chemical compound C[Si](C)(C)C(C(N)=O)[Si](C)(C)C NDVMCQUOSYOQMZ-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000005051 trimethylchlorosilane Substances 0.000 description 2
- BEEYLGLWYXWFAG-UHFFFAOYSA-N 2-aminosilyl-2-methylpropane Chemical compound CC(C)(C)[SiH2]N BEEYLGLWYXWFAG-UHFFFAOYSA-N 0.000 description 1
- LINZZISWCNKFEM-UHFFFAOYSA-N 3,3-dimethylbutanamide Chemical compound CC(C)(C)CC(N)=O LINZZISWCNKFEM-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- UJMWUVWZCDUPPH-UHFFFAOYSA-N 5-silyl-2H-1,3-oxazol-2-id-4-one Chemical class [SiH3]C1C(N=[C-]O1)=O UJMWUVWZCDUPPH-UHFFFAOYSA-N 0.000 description 1
- 101100177155 Arabidopsis thaliana HAC1 gene Proteins 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical class O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 239000005046 Chlorosilane Substances 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- KXNOLRHLPNEOLX-UHFFFAOYSA-N N-tert-butyl-N,2-dimethyl-2-silylpropanamide Chemical compound CC(C)(C)N(C)C(=O)C(C)(C)[SiH3] KXNOLRHLPNEOLX-UHFFFAOYSA-N 0.000 description 1
- 101100434170 Oryza sativa subsp. japonica ACR2.1 gene Proteins 0.000 description 1
- 101100434171 Oryza sativa subsp. japonica ACR2.2 gene Proteins 0.000 description 1
- 101150108015 STR6 gene Proteins 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- SIOVKLKJSOKLIF-UHFFFAOYSA-N bis(trimethylsilyl)acetamide Chemical compound C[Si](C)(C)OC(C)=N[Si](C)(C)C SIOVKLKJSOKLIF-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- BUMGIEFFCMBQDG-UHFFFAOYSA-N dichlorosilicon Chemical compound Cl[Si]Cl BUMGIEFFCMBQDG-UHFFFAOYSA-N 0.000 description 1
- JJQZDUKDJDQPMQ-UHFFFAOYSA-N dimethoxy(dimethyl)silane Chemical compound CO[Si](C)(C)OC JJQZDUKDJDQPMQ-UHFFFAOYSA-N 0.000 description 1
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 1
- CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical group Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- GYLDXXLJMRTVSS-UHFFFAOYSA-N n-butylacetamide Chemical compound CCCCNC(C)=O GYLDXXLJMRTVSS-UHFFFAOYSA-N 0.000 description 1
- ACYFWRHALJTSCF-UHFFFAOYSA-N n-tert-butylacetamide Chemical compound CC(=O)NC(C)(C)C ACYFWRHALJTSCF-UHFFFAOYSA-N 0.000 description 1
- LWFWUJCJKPUZLV-UHFFFAOYSA-N n-trimethylsilylacetamide Chemical group CC(=O)N[Si](C)(C)C LWFWUJCJKPUZLV-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
Definitions
- Silylamides are known from U.S. Pat. No. 2,876,209 which shows the preparation of amidosilanes by reacting an aminosilane of the formula R 4-x Si(NR'R") y , with amides with the removal of the amine by-product by volatilization.
- the amidosilanes produced are of the formula ##STR3##
- WHERE R' can be alkyl of 1 to 18 carbon atoms such as methyl, ethyl, butyl, etc.
- this patent has no specific disclosure of an N-t-butylamide either in column 4, line 52, or lines 58-68 where the various groups substituted on the nitrogen are elucidated.
- a t-butylsilylamine is one of the starting materials but the t-butyl group is removed as t-butyl amine by volatilization.
- U.S. Pat. No. 2,876,234 which claims the amidosilanes.
- U.S. Pat. No. 3,436,415 discloses the compound allylethylbis-N-isopropyl-propionamidesilane, column 2, line 39, and its use as an intermediate in the preparation of silyloxazolidones.
- U.S. Pat. No. 3,488,371 discloses the compound phenylmethylbis-N-(beta-phenylisopropyl)acetamidosilane (Example 5). None of these references, however, disclose the N-t-butyl derivative of these amidosilanes.
- amidosilanes and various other reactive silanes are silylating agents which are extensively used in reaction with organic or inorganic molecules containing the hydroxyl, the NH or the SH group.
- these silylations are carried out in order to modify the starting compounds either in order to carry out additional synthetic steps or in order to modify complex mixtures so that they can be more easily separated. Additional reasons for silylation are to modify surfaces of materials in order to render them hydrophobic and organophilic.
- the compounds of this invention can be used for silylating any compound containing the OH, NH, SH or carboxyl group. They are particularly useful in silylating unreactive compounds such as ureas and in the silylation of complex mixtures.
- This invention relates to compounds of the formula ##STR4## where n is 2 or 3, R is of the group methyl, ethyl, vinyl, phenyl or 3,3,3-trifluoropropyl at least 2 R's being methyl when n is 3 and R' is methyl or ethyl.
- compositions of this invention are more complex than the simple formula shown above. It is generally believed that silylated amides are actually an equilibrium mixture of tautomeric materials represented by the equation ##STR5## In other words, it is believed that the compounds are mixtures of the amide and imidate form of these materials. Consequently, it should be understood that this application and the claims in this application cover both forms of the molecules and mixtures thereof.
- compositions of this invention where n is 3 are best prepared by reacting the chlorosilane of the formula R 3 SiCl with the corresponding N-t-butylamide in the presence of a tertiary amine as a hydrogen halide acceptor. This reaction proceeds readily at room temperature and the amine hydrochloride salt is removed by filtration or other suitable means and the silylated amide is obtained by distillation or other suitable means.
- the compositions of this invention where n is 2 are best prepared by reacting a silane of the formula R 2 SiCl 2 with the corresponding compound ##STR6## under conditions where the triorganochlorosilane is removed from the reaction zone. This reaction will generally occur at ambient temperature and the R 3 SiCl can be removed at reduced pressure.
- a dry flask was fitted with a reflux condenser, stirring bar and septum and evacuated and flushed with dry nitrogen. The flask was protected from moisture with nitrogen and a series of dry ice traps. The flask was charged with 20 g. of sublimed N-t-butylacetamide, 118.39 g. of triethylamine and 50 ml. of dry pentane. 37.73 g. of trimethylchlorosilane was added to the stirred solution through a syringe. A slight exotherm was noted along with the precipitation of triethylamine hydrochloride. The mixture was allowed to stir overnight and the slurry was centrifuged.
- the amount of D produced at equilbrium is a measure of the reactive reactivity of A with respect to D and the reactivity of A is a function of the equilibrium constant K/eg.
- K/eg equilibrium constant
- the gas liquid chromatograms were taken on an Infotronics Model 2400 Series gas chromatograph equipped with a Model 68 linear temperature programmer and a 6 ft. by 1/8 inch (182.88 cm. by 3.18 mm) packed with diatomaceous earth of 100 to 120 mesh coated with 5% by weight of a trifluoropropylmethyl siloxane of 10,000 cs viscosity (designated SP-2401 by Supelco Incorporated).
- the injection port temperature was maintained at 200° C and the detector (He) at 310° C.
- the column was linearly programmed at 20° C/min. from 100° to 200° C with a chart speed of 2 min./inch. (2.45 cm).
- Runs 2 to 5 are for purpose of comparison.
- N-t-butyltrimethyl-silylacetamide of this invention is 5 times faster than the best previously known silylating agent (2); is 110 times faster than the corresponding n-butyl compound (3); is 366 times faster than the N-methyl compound (4); and is 100,000 times faster than the N-isopropyl derivative (5).
- Example 1 Using the procedure of Example 1, the following compounds can be prepared by reacting the following silanes with the following N-t-butylamides.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/858,144 US4107196A (en) | 1977-12-07 | 1977-12-07 | N-tertiarybutyl organosilylamides |
| CA305,390A CA1112656A (fr) | 1977-12-07 | 1978-06-13 | Organosilylamides de n-butyl tertiaire |
| GB7828011A GB2009769B (en) | 1977-12-07 | 1978-06-27 | N-tertiarybutyl organosilylamides |
| DE2829389A DE2829389C3 (de) | 1977-12-07 | 1978-07-04 | Organosilylamide |
| JP9812378A JPS5479233A (en) | 1977-12-07 | 1978-08-11 | Silylamide composition |
| FR7834339A FR2411201B1 (fr) | 1977-12-07 | 1978-12-06 | N-tert-butyl-organosilylamides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/858,144 US4107196A (en) | 1977-12-07 | 1977-12-07 | N-tertiarybutyl organosilylamides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US4107196A true US4107196A (en) | 1978-08-15 |
Family
ID=25327600
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US05/858,144 Expired - Lifetime US4107196A (en) | 1977-12-07 | 1977-12-07 | N-tertiarybutyl organosilylamides |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4107196A (fr) |
| JP (1) | JPS5479233A (fr) |
| CA (1) | CA1112656A (fr) |
| DE (1) | DE2829389C3 (fr) |
| FR (1) | FR2411201B1 (fr) |
| GB (1) | GB2009769B (fr) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0165509A1 (fr) * | 1984-06-09 | 1985-12-27 | Bayer Ag | Procédé d'amélioration de la solubilité de certains composés organiques qui sont difficilement solubles dans les solvants inertes par silylation avec le cyanure de crialkylsilane |
| WO2019042883A1 (fr) | 2017-08-31 | 2019-03-07 | Umicore Ag & Co. Kg | Catalyseur adsorbant passif d'oxyde d'azote à base de palladium-zéolite pour la purification de gaz d'échappement |
| WO2019042884A1 (fr) | 2017-08-31 | 2019-03-07 | Umicore Ag & Co. Kg | Utilisation d'un catalyseur à base de palladium-platine-zéolite en tant qu'adsorbant passif d'oxyde d'azote pour la purification de gaz d'échappement |
| WO2019134958A1 (fr) | 2018-01-05 | 2019-07-11 | Umicore Ag & Co. Kg | Adsorbeur d'oxyde d'azote passif |
| EP3824988A1 (fr) | 2019-11-20 | 2021-05-26 | UMICORE AG & Co. KG | Catalyseur pour la réduction d'oxydes d'azote |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2876234A (en) * | 1955-06-01 | 1959-03-03 | Rohm & Haas | Organic silicon compounds and methods for making them |
| US2876209A (en) * | 1955-06-01 | 1959-03-03 | Rohm & Haas | Organic silicon compounds and methods for making them |
| US2906756A (en) * | 1955-06-01 | 1959-09-29 | Rohm & Haas | New organic silicon compounds and methods of making them |
| US3488371A (en) * | 1967-08-18 | 1970-01-06 | Gen Electric | Linear difunctional silylamide and process therefor |
| US3776933A (en) * | 1972-09-29 | 1973-12-04 | Dow Corning | Method of preparing amidosilanes |
| US3954651A (en) * | 1973-12-20 | 1976-05-04 | Macherey, Nagel & Company | Silyation agent for gas chromatography |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3397220A (en) * | 1964-05-28 | 1968-08-13 | Gen Electric | Silylating process and agent |
-
1977
- 1977-12-07 US US05/858,144 patent/US4107196A/en not_active Expired - Lifetime
-
1978
- 1978-06-13 CA CA305,390A patent/CA1112656A/fr not_active Expired
- 1978-06-27 GB GB7828011A patent/GB2009769B/en not_active Expired
- 1978-07-04 DE DE2829389A patent/DE2829389C3/de not_active Expired
- 1978-08-11 JP JP9812378A patent/JPS5479233A/ja active Granted
- 1978-12-06 FR FR7834339A patent/FR2411201B1/fr not_active Expired
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2876234A (en) * | 1955-06-01 | 1959-03-03 | Rohm & Haas | Organic silicon compounds and methods for making them |
| US2876209A (en) * | 1955-06-01 | 1959-03-03 | Rohm & Haas | Organic silicon compounds and methods for making them |
| US2906756A (en) * | 1955-06-01 | 1959-09-29 | Rohm & Haas | New organic silicon compounds and methods of making them |
| US3488371A (en) * | 1967-08-18 | 1970-01-06 | Gen Electric | Linear difunctional silylamide and process therefor |
| US3776933A (en) * | 1972-09-29 | 1973-12-04 | Dow Corning | Method of preparing amidosilanes |
| US3954651A (en) * | 1973-12-20 | 1976-05-04 | Macherey, Nagel & Company | Silyation agent for gas chromatography |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0165509A1 (fr) * | 1984-06-09 | 1985-12-27 | Bayer Ag | Procédé d'amélioration de la solubilité de certains composés organiques qui sont difficilement solubles dans les solvants inertes par silylation avec le cyanure de crialkylsilane |
| WO2019042883A1 (fr) | 2017-08-31 | 2019-03-07 | Umicore Ag & Co. Kg | Catalyseur adsorbant passif d'oxyde d'azote à base de palladium-zéolite pour la purification de gaz d'échappement |
| WO2019042884A1 (fr) | 2017-08-31 | 2019-03-07 | Umicore Ag & Co. Kg | Utilisation d'un catalyseur à base de palladium-platine-zéolite en tant qu'adsorbant passif d'oxyde d'azote pour la purification de gaz d'échappement |
| US11141717B2 (en) | 2017-08-31 | 2021-10-12 | Umicore Ag & Co. Kg | Palladium/zeolite-based passive nitrogen oxide adsorber catalyst for purifying exhaust gas |
| US11161100B2 (en) | 2017-08-31 | 2021-11-02 | Umicore Ag & Co. Kg | Use of a palladium/platinum/zeolite-based catalyst as passive nitrogen oxide adsorber for purifying exhaust gas |
| WO2019134958A1 (fr) | 2018-01-05 | 2019-07-11 | Umicore Ag & Co. Kg | Adsorbeur d'oxyde d'azote passif |
| EP3824988A1 (fr) | 2019-11-20 | 2021-05-26 | UMICORE AG & Co. KG | Catalyseur pour la réduction d'oxydes d'azote |
| WO2021099361A1 (fr) | 2019-11-20 | 2021-05-27 | Umicore Ag & Co. Kg | Réacteur de réduction d'oxydes d'azote |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5479233A (en) | 1979-06-25 |
| DE2829389A1 (de) | 1979-06-13 |
| DE2829389B2 (de) | 1981-07-30 |
| CA1112656A (fr) | 1981-11-17 |
| FR2411201A1 (fr) | 1979-07-06 |
| JPS5753799B2 (fr) | 1982-11-15 |
| DE2829389C3 (de) | 1982-05-19 |
| FR2411201B1 (fr) | 1985-12-13 |
| GB2009769A (en) | 1979-06-20 |
| GB2009769B (en) | 1982-08-18 |
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